Start planning your fall getaway to Boothbay Harbor, Maine, and the Flagship Inn. Our property is a centrally located, offering the perfect gateway to fall festivals in Midcoast Maine! Whether you are looking for family-friendly fun, pumpkin-themed events, or fall foliage train rides, there is something for everyone in your group.
Damariscotta Pumpkinfest & Regatta
In early October, take the short drive to Damariscotta (and neighboring Newcastle) to see intricately carved and decorated giant pumpkins, designed each year by local Maine artists. Attend the pumpkin weigh off to see who will win first place under several categories.
Don’t miss the regatta on the river! Watch as competitors paddle and race in hollowed-out, giant, festively adorned pumpkins for a chance at the title. In addition to decorated pumpkins and the regatta, check out the pumpkin derby, dessert and pie-eating contests, the infamous pumpkin drop and a parade through downtown.
Fall Foliage Festival
Head over to the Boothbay Railway Village for their annual Fall Foliage Festival. Explore the historic buildings, built in the early 1900s, and be sure to spend some time at the antique car museum, and model railroad. This festival features delicious food, arts and crafts, live music and entertainment, steam train rides, and colorful fall foliage across 4-acres! Perfect for all ages; a family outing that just might become an annual tradition.
Scenic Drive through Midcoast Maine
Go for a scenic drive or hike a nature preserve, and take in the fall colors across the Midcoast region. Don’t forget your phone to snap photos along the way… be sure to take a look at the Fall Foliage report to see when peak season hits across the state of Maine.
Southern Maine (Zone 1)
Covers Mid-Coast and South Coastal Maine, including Boothbay, Camden, Portland, Kennebunkport and Kittery
Projected Peak Foliage Week: Mid to Late October
Plan your trip to the Flagship Inn, join us for fall festivals, scenic tours, and giant pumpkins near our Boothbay Harbor inn. Call our Front Desk at (207) 633-5094 to book your stay or click below to book direct today!
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